Announcing American Sailing’s 2023 Outstanding Instructors

By: Instructors

American Sailing is a vibrant community of sailors, sailing schools, and individuals with a passion for spending more time on the water. At the heart of this community are our American Sailing Instructors, who play a pivotal role in shaping the sailing experience. They not only introduce you to the community but also guide you through the process of becoming familiar with your surroundings.

Your experience with sailing as a first-timer is dictated by the knowledge that our instructors impart, and as you grow in the sport, the experience of our instructors propels you to achieve your goals.

Our American Sailing Instructors are the backbone of our organization, and their dedication and expertise have made us the strong and proud community we are today.  


 … We celebrate and honor our outstanding instructors each year, recognizing the top 1% of active ASA instructors


This prestigious award is a testament to their skill and a reassurance to you, our sailors, of the quality of instruction you can expect.

Of the 2,566 Instructors in 2023 who had active status, 943 taught at least one ASA class and thereby became eligible for this ASA Award. The top 30, a diverse group representing 28 cities across 16 states and 3 countries, are listed below. This diversity reflects our commitment to inclusivity and our belief that sailing is for everyone.


Jim King, owner of North Star Sailing Charters in Biloxi, Mississippi, discovered his passion for sailing in 2006, quickly buying a boat and immersing himself in the sport. His sailing adventures have taken him from Jacksonville, Florida, to England, and during his Air Force service, to the Potomac River and Chesapeake Bay.

What do people not know about sailing that they should? 

“It is not difficult to do and a great way to relax.  I think too many instructors get too wrapped up in the technical details of being “perfect” sailors.  Nothing wrong with being a “casual” sailor…all the fun without all the worry about perfection.”



Captain Emory Heisler has been sailing for over 30 years and is an influential leader in the Arizona sailing community, having served as commodore of the Arizona Yacht Club and as the current president of the Arizona Sailing Foundation (ASF)

Why do you sail?

“The people. The presentness. The constant learning. The combination of simplicity and complexity, peacefulness and terror, and the ever-changing interplay of technology and nature. It’s ADHD heaven.”



Captain Jennifer MacLean, known as Captain Jenn, is an award-winning sailing instructor and charter yacht captain with over 20 years of experience. Jenn specializes in women’s, couples, and youth sailing programs and has lived aboard her boat for 18 years. She has extensive sailing experience, including Atlantic Ocean crossings and solo sails to the Bahamas.

“Every class I teach becomes memorable in its own way. Every trip is different but amazing. I love teaching live aboard courses so people really get the feel of living aboard and to see if that’s for really them before even buying a boat.”



Captain Joe Mastrangelo is a veteran and native of Miami, FL who has been sailing, diving and spearfishing the waters of the Florida Keys/Bahamas for over 30 years. As a US Navy SEAL and Government contractor, he has traveled the world gaining a unique insight into humanities needs and desires.

Why should people sail?

“People should sail to completely reconnect with nature – period. We have become so engrossed with technology, that we are rapidly losing our spiritually ingrained balance with nature. Look around you – faces buried in phones, constantly inundating one’s mind with the current “news”.  Technology can bring great advances in certain fields however, don’t bear away from man’s true course; that of spiritual development.”



Captain Bob is an experienced sailing instructor and charter yacht captain with over 25 years of experience. Known for his patient teaching style, he enjoys making sailing accessible for all skill levels. Off the water, he enjoys kayaking, fishing, and storytelling about his adventures.

Why should people sail?

“For the time of their life. It is something they will never forget. The peacefulness of the water going by the hull, the wind on your face, the feeling of being out on the water and it’s you, the sea, and the wind taking you to your destination. How cool is that?”



Captain Mike Nyakas grew up on the ocean in Prince Rupert, commercially fished as a youth, and spent his adult career in the hospitality industry and Corporate Sales. Mike believes the best environment for learning is allowing nature and the sailboat to present the best platform in a relaxed way while enjoying all aspects of the cruising lifestyle… after all, someone has to snorkel, paddleboard and visit these amazing anchorages.

What is your favorite place to sail?

“BC of course.. It boasts incredible coastlines with endless exploration, offering a vast playground for sailors. From the dramatic fjords and snow-capped mountains of the north to the sheltered islands and sandy beaches of the south, there’s a unique sailing experience for everyone.”



Captain Clay Dingledine is a native to Virginia’s Northern Neck and first began his sailing adventures on his high school racing team. With an adventurous soul, he moved to other cities, countries and even land-locked states but the shores of the Chesapeake Bay always beckoned him home.

Why Should People Sail?

“People should sail for so many reasons. It is challenging and doing challenging things provides a sense of accomplishment that can be so rewarding and ultimately, I think, promotes well-being.  Also there is bliss to be had in sailing.  Whether you get it from the competition in racing or the ease and relaxation of a sunset cruise, I think we all deserve to do the things in life that inspire us.”


This year there are 13 first-time Outstanding Instructors of the Year indicated by a star icon.

Trevon BakerSomers, MT, USA
Daniel BrittHolland, NY, USA
Michael ClidasOlympia, WA, USA
Richard DahlinCapistrano Beach, CA, USA
Andrew DeenTampa, FL, USA
Claiborne DingledineWeems, VA, USA
Riley DunnCharleston, SC, USA
Jeremy ElwellPanama City, FL, USA
Brian GwinnupNiceville, FL, USA
Raymond Emory HeislerChandler, AZ, USA
Thomas Herrington IIICharleston, SC, USA
Timothy JenneSequim, WA, USA
James KingGulfport, MS, USA
Bob LaBineGreen Cove Springs, FL, USA
Qing LiShanghai, China
Jennifer MacLeanTavernier, FL, USA
Joseph MastrangeloKey Largo, FL, USA
Vincent MattiolaLewes, DE, USA
Christopher MayKey West, FL, USA
Andrew McCabeCarrying Place, ON, CANADA
George NorwoodRiverview, FL, USA
Michael NyakasVancouver, BC, CANADA
John O’Neal IIISolana Beach, CA, USA
Chris StaleyLusby, MD, USA
William SutherlandBloomfield Hills, MI, USA
Richard Van LoonShrewsbury, NJ, USA
Brian VanWierenMunising, MI, USA
Charles VaughnKey Largo, FL, USA
Jennifer WirthMiami, FL, USA
Elliot ZimmermanLos Angeles, CA, USA